Looking at this question, I wanted to give a different perspective...
The bottom line is - it's all about you.
I agree with the other posters that work, passion and choice, advancement, cohesion and passion are all reasons that I, personally, would stay or leave a given job. But even more important is how you assess your work and what you see as a plus or a minus. And also by how much you care. And how much better you could or couldn't do in the marketplace right now. You always want the best job (for you) that you can possibly get without too much long term harm to your overall career. Taking those parts part, it's
The best job right now
That's knowing the market and having been in enough recent interviews to know how you rank. I'd advise interviewing and applying to interesting opportunities every few years, just so you know where you rate in the market. Or doing something else that gives you an idea of what your options might be.
Also - scanning job sites and talking to peers will give you an idea of whether those other jobs are really something you'd like - getting the details from someone you trust is always helpful.
Long term career
There's a number of tradeoffs that are awesome in the short term, but perhaps bad in the long term... examples (for me) would be:
- Job hopping more than every 3 years. I hate change, I don't feel like I really know my job until I've been at it a while, and in my line of work, I look down on people who don't give a new place a decent trial, so I don't want to have a resume with a lot of job changes.
- Good money, bad challenges - the jobs that pay very good salaries to work on technologies that will be hard to transition to other businesses.
- Great money, horrible work conditions - I'm thinking of conditions so bad they would affect your long term health.
Note - even these are personal - a person at the end of their career may not care so much about deprecated technologies, particularly if they think there will be a great golden handshake at the end of the work.
Similarly - my metric of 3 years is specific to me... mileage varies.
Best job for you
The most specific of all... many of the cons you mention, I would see as opportunities... so my response is, that these cons are a big deal if you think they are... A lot of your examples come from a weakly structured office that doesn't seem to have much growth or guidance. If you've been working there for 8 years, that's unlikely to change. Some people may see the vagueness you mention as an opportunity to develop their own path. Others will find it debilitatingly frustrating.
I've seen people stick with what I would think of as a lame job for all sorts of personal reasons - and it's hard to argue that family, kids, the commute, or a particular perk is a deciding force that overcomes all sorts of other frustration when figuring out priorities.